Categories: C-C Bond Formation > Heteroatom-containing Molecules > Trihalomethyl Carbinols
Synthesis of tribromomethyl carbinols
Recent Literature
Trihaloacetic acids can been converted to trichloromethyl and tribromomethyl ketones in good
yield by a catalyzed reaction with aldehydes followed by oxidation. A coupling of organozinc intermediates with trichloroacetyl chloride
gives trichloromethyl ketones.
E. J. Corey, J. O. Link, Y. Shao, Tetrahedron Lett., 1992,
33, 3435-3438.
TiCl4-Mg mediates the addition of CHBr3 or CBr3
depending on the reaction conditions to various aldehydes and ketones to form
dibromomethyl carbinols and tribromomethyl carbinols respectively. The
successful application of TiCl4-Mg-promoted coupling of CHBr3
with highly enolizable ketones such as 2-indanone and β-tetralone highlights the
extraordinary reactivity and selectivity and the weakly basic nature of this
system.
T.-H. Yan, S.-H. Chang, C.-T. Chang, C.-K. Lin, C.-Y. Liu, Org. Lett., 2013,
15, 5802-5805.